Yellow mono-azodyestuffs capable of being chromed



Patented Dec. 10, 1935 UNITED STATES PATENT OFFICE YELLOW MONO-AZODYESTUFFS CAPABLE OF BEING CHROMLED Erich Fischer, Bad Soden-on-the-Taunus, and

Herbert Kracker, Frankfort-on-the-Main, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application November '7, 1933, Serial No. 697,080. In Germany November 15,

4 Claims.

The present invention relates to yellow monoazo-dyestufis capable of being chromed; more particularly it relates to dyestuffs of the following general formula:

carboxylic acid or 5-chloro-2-aminobenzene-1- carboxylic acid with pyrazolone derivatives, according to the statements of U. S. Patent No. 1,149,231, the dyestufis of the'present invention are distinguished by a better fastness to light. This unequivocal effect of the 3-halogen-anthranilic acids could not be foreseen and represents a considerable technical advance, especially with regard to the fact that the dyestufis possess besides their very good fastness to light a very good leveling power as well as a very good fastness to washing and to fulling.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight:

(1) 171.5 parts of 3-chloro-2-aminobenzene-lcarboxylic acid are diazotized in the usual manner. The diazo-solution is gradually run into a solution of 254 parts of 1(4'-sulfophenyl)-3- formula:

methyl-5-pyrazolone in sodium carbonate solution. When the coupling is finished, the dyestufi is precipitated with common salt in the usual manner, filtered by suction and dried. It forms a yellow powder which dyes wool from an acid bath yellow tints which, when after-chromed, are distinguished by a very good fastness to washing, to iulling and to light.

The dyestuff possesses the following formula:

son; 10

(2) 288.5 parts of 1-(2'-ch1oro-5-su1fophenyl)-3-methyl-5-pyrazolone are dissolved in water and sodium carbonate to form a neutral solution, and a, solution of parts of sodium acetate is added thereto. Into the thus prepared coupling-solution there is. run a vdiazo-solution from 226 parts of 3-bromo-2-aminobenzene-lcarboxylic acid. The dyeings which this dyestuff yields on wool, possess, when after-chromed, a more greenish hue but, otherwise, the same fastness properties as those of the dyestuff obtained according to the statements of Example 1.

The dyestuii corresponds with the following the pyrazolones mentioned therein 394 parts of a. pyrazolone of the following constitution:

- 1-(2',5 dichloro 4 sulfophenyl) 3 methyl- 5-pyrazolone, 1-(4'-chloro-2-sulfophenyl) 3 methyI-S-pyrazolone, 1 (2- hydroXy-3-carboxy-5-sulfophenyl) 3 methyl-5-pyrazolone, 1- (4-methyl-2'-sulfophenyl) -3 methyl 5 -pyrazolone, 1 (f-sulfophenyl) -5-pyrazolone-3- carboxylic acid-ethyl ester, 1-(4-sulfonaphthyl) -3-methyl-5-pyrazolone,

furthermore, by pyrazolone derivatives of, for instance, the following constitution:

COOH

The following table indicates a number of dyestuffs obtainable according to the present invention, but does not comprise all possibilities for the preparation of dyestuffs of very good fastness to light by using other pyrazolone derivatives and other 3 halogen-2-aminobenzene-l-carboxylic acids; it, therefore, is not intended to limit the invention to the dyestuffs mentioned therein:

We claim: 1. The mono-azodyestuffs of the general formula:

/ coon 5 wherein R represents a radical of the benzene series, forming, when dry, yellow powders and yielding on wool yellow dyeings which, when after-chromed, possess very good fastness properties, particularly a very good fastness to light.

3. The mono-azodyestufi of the following formula:

forming, when dry, a yellow powder and yielding 50 on wool a yellow dyeing which, when after- Diazo component from Coupling component Tint 1 3-chlgro-2-aminobenzene-l-carboxylic 1-1(3'-sulfopheny1)-3-methyl-5-pyrazo- Greenlsh-yellow.

1.01 0118. 2 do l-1(2"sulfopheny1)-3-methyl-5-pyrazo- Do one. 3 do 1-(2,4-dichloro-6'-sul(ophenyl)-3- Do.

methy1-5-pyrazolone. 4 3-bromo-2-aminobenzene-l-carboxylic 1-(4-sul ophenyl)-5-pytazo1one-3-car- Yellow.

acld. boxylic acid-ethyl-oster. 60

6 3-chlgro-2-aminobenzene-l-carboxylic OC H| Do.

N C==O II a H;CG- H;

6 -.do 1-(3-sul fophenyl)-5-pyrazolone-3-car- Do.

boxyllc acld-methyl-ester. 7 3-bromo-2-aminobenzene-l-carboxyhc 1-(4'-chloro-2'-sullophenyl)-5-pyrazo- Do;

ac lone-3'carboxylic acid-butyl-ester. 8 3-ehloro-2-am1nobenzenc-l-carboxylic 1 (2'-cbloro -5-sulfophenyl) -5-pyrazo- Do.

ac 1one-3-carboxylic acid-ethyl-ester. 7 0

chromed, possesses a. very good tastness to washing, fulling and light.

4. The mono-azodyestufl' of the following formula:

forming. when dry, 9. yellow powder and yielding on wool a yellow dyeing which, when after- 

